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33947220481
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Zinc(II) tetrakis({2-Deoxy-3,5-bis[O-(p-toluoyl, α,β- D-ribofuranosyl}ethynyl) phthalocyaninate (4, A mixture of 2 17 (250.0 mg, 0.231 mmol, 316 (524.8 mg, 1.39 mmol, Pd(PPh3)2Cl2 (20 mg) and CuI (10 mg) were dried under vacuum for 1 h. To this mixture, anhyd DMF (2.5 mL) was added followed by Et3N (1 mL) and allowed to stir at r.t. for 72 h. The solvent was removed by evaporation and the crude green solid was purified by silica gel chromatography (EtOAc-hexane, 40:60) to furnish 4 as a blue solid (360.0 mg, 75, IR (KBr, 2954, 2229, 1720, 1611, 1488, 1386, 1271, 1178, 1100, 1020, 837, 752 cm-1; 1H NMR (600MHz, acetone-d6, δ, 8.64 (br s, 8 H, Ar-H, 8.23-8.06 (m, 20 H, Ar-H, 7.42-7.37 (m, 16 H, Ar-H, 5.87-5.56 (m, 8 H, 1′,3′-H, 4.95-4.71 (m, 12 H, 4′,5′-H, 3.11-2.98 m, 8 H, 2′-H, 2.46-2
-
4].
-
-
-
-
61
-
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33947238455
-
-
Zinc(II) tetrakis[(2-deoxy-α,β-D-ribofunosyl)ethynyl] phthalocyaninate (1, A mixture of 4 (20.1 mg, 0.0096 mmol, and K2CO3 (14.4 mg, 0.104 mmol, in MeOH-THF (2:1, 3 mL) was stirred at r.t. for 48 h. The reaction mixture was filtered and washed with MeOH. The MeOH was evaporated off to furnish a dark blue solid, to which was added H2O (4.0 mL, pH adjusted to 6) and filtered. The solid was washed with H2O and 30% of acetone in H2O and purified twice by Sephadex® G-25 using MeOH as an eluent. Evaporation of the solvent gave a crude blue solid. Further purification by recrystallization with MeOH and EtOAc gave pure 1 (8.2 mg, 80, IR (KBr, 2954, 2229, 1720, 1611, 1488, 1386, 1271, 1178, 1100, 1020, 837, 752 cm-1; 1H NMR (600MHz, CD3OD, δ, 8.54 (br s, 8 H, Ar-H, 7.91 (br s, 4 H, Ar-H, 5.31 (br s, 4 H, 1′-H, 4.52 (br s, 2 H, 4′-H, 4.43 br s
-
-5 M).
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-
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62
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0000445152
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31044456860
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Krausz, P.8
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